RU2448937C2 - Способ превращения этилбензола и способ получения пара-ксилола - Google Patents
Способ превращения этилбензола и способ получения пара-ксилола Download PDFInfo
- Publication number
- RU2448937C2 RU2448937C2 RU2008142763/04A RU2008142763A RU2448937C2 RU 2448937 C2 RU2448937 C2 RU 2448937C2 RU 2008142763/04 A RU2008142763/04 A RU 2008142763/04A RU 2008142763 A RU2008142763 A RU 2008142763A RU 2448937 C2 RU2448937 C2 RU 2448937C2
- Authority
- RU
- Russia
- Prior art keywords
- xylene
- ethylbenzene
- isomerization
- specified
- separation
- Prior art date
Links
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 title claims abstract description 190
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 title claims abstract description 163
- 238000000034 method Methods 0.000 title claims abstract description 83
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 195
- 239000003054 catalyst Substances 0.000 claims abstract description 95
- 238000006243 chemical reaction Methods 0.000 claims abstract description 86
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 81
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 63
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 claims abstract description 42
- 229910052751 metal Inorganic materials 0.000 claims abstract description 29
- 239000002184 metal Substances 0.000 claims abstract description 29
- 150000002739 metals Chemical class 0.000 claims abstract description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 116
- 239000008096 xylene Substances 0.000 claims description 115
- 238000006317 isomerization reaction Methods 0.000 claims description 99
- 238000000926 separation method Methods 0.000 claims description 70
- 230000006204 deethylation Effects 0.000 claims description 54
- 238000004821 distillation Methods 0.000 claims description 42
- 239000010457 zeolite Substances 0.000 claims description 42
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 40
- 229910021536 Zeolite Inorganic materials 0.000 claims description 35
- 239000002994 raw material Substances 0.000 claims description 27
- 239000007795 chemical reaction product Substances 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 15
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 15
- 229910052702 rhenium Inorganic materials 0.000 claims description 11
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 11
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 238000012545 processing Methods 0.000 claims description 4
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 31
- 230000000694 effects Effects 0.000 abstract description 9
- 239000000126 substance Substances 0.000 abstract description 4
- 238000009835 boiling Methods 0.000 description 51
- 239000000047 product Substances 0.000 description 42
- 150000004706 metal oxides Chemical class 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 11
- 238000000605 extraction Methods 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 238000005342 ion exchange Methods 0.000 description 10
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- -1 cycloparaffins Chemical class 0.000 description 9
- 238000006900 dealkylation reaction Methods 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 8
- 238000006555 catalytic reaction Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000009616 inductively coupled plasma Methods 0.000 description 7
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- 238000007323 disproportionation reaction Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 6
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 238000004611 spectroscopical analysis Methods 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 229910004298 SiO 2 Inorganic materials 0.000 description 5
- 150000001491 aromatic compounds Chemical class 0.000 description 5
- 230000020335 dealkylation Effects 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 238000001179 sorption measurement Methods 0.000 description 5
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910001424 calcium ion Inorganic materials 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000004891 communication Methods 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- 238000010555 transalkylation reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000003738 xylenes Chemical class 0.000 description 4
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- 239000003463 adsorbent Substances 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002407 reforming Methods 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 238000001354 calcination Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229960001484 edetic acid Drugs 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 229940078552 o-xylene Drugs 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910001388 sodium aluminate Inorganic materials 0.000 description 2
- 239000011973 solid acid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 1
- JRLPEMVDPFPYPJ-UHFFFAOYSA-N 1-ethyl-4-methylbenzene Chemical compound CCC1=CC=C(C)C=C1 JRLPEMVDPFPYPJ-UHFFFAOYSA-N 0.000 description 1
- ZLCSFXXPPANWQY-UHFFFAOYSA-N 3-ethyltoluene Chemical compound CCC1=CC=CC(C)=C1 ZLCSFXXPPANWQY-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- VXAUWWUXCIMFIM-UHFFFAOYSA-M aluminum;oxygen(2-);hydroxide Chemical group [OH-].[O-2].[Al+3] VXAUWWUXCIMFIM-UHFFFAOYSA-M 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000006200 ethylation reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical class CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000004876 x-ray fluorescence Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/2702—Catalytic processes not covered by C07C5/2732 - C07C5/31; Catalytic processes covered by both C07C5/2732 and C07C5/277 simultaneously
- C07C5/2724—Catalytic processes not covered by C07C5/2732 - C07C5/31; Catalytic processes covered by both C07C5/2732 and C07C5/277 simultaneously with metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
- C07C4/08—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule
- C07C4/12—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene
- C07C4/14—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene splitting taking place at an aromatic-aliphatic bond
- C07C4/18—Catalytic processes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
- B01J29/48—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively containing arsenic, antimony, bismuth, vanadium, niobium tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
- C07C15/04—Benzene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
- C07C15/067—C8H10 hydrocarbons
- C07C15/08—Xylenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/2702—Catalytic processes not covered by C07C5/2732 - C07C5/31; Catalytic processes covered by both C07C5/2732 and C07C5/277 simultaneously
- C07C5/2708—Catalytic processes not covered by C07C5/2732 - C07C5/31; Catalytic processes covered by both C07C5/2732 and C07C5/277 simultaneously with crystalline alumino-silicates, e.g. molecular sieves
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/10—After treatment, characterised by the effect to be obtained
- B01J2229/18—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself
- B01J2229/186—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself not in framework positions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
- C07C2529/48—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11 containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
- C07C2529/78—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65 containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006-091948 | 2006-03-29 | ||
JP2006091948 | 2006-03-29 |
Publications (2)
Publication Number | Publication Date |
---|---|
RU2008142763A RU2008142763A (ru) | 2010-05-10 |
RU2448937C2 true RU2448937C2 (ru) | 2012-04-27 |
Family
ID=38563396
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU2008142763/04A RU2448937C2 (ru) | 2006-03-29 | 2007-03-28 | Способ превращения этилбензола и способ получения пара-ксилола |
Country Status (8)
Country | Link |
---|---|
US (1) | US20100179360A1 (ko) |
EP (1) | EP2008988A4 (ko) |
KR (1) | KR101357387B1 (ko) |
CN (1) | CN101410354B (ko) |
MY (1) | MY153671A (ko) |
RU (1) | RU2448937C2 (ko) |
TW (1) | TWI432409B (ko) |
WO (1) | WO2007114127A1 (ko) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2514423C1 (ru) * | 2010-03-31 | 2014-04-27 | Юоп Ллк | Способ изомеризации ксилола и этилбензола с использовнием uzm-35 |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7939701B2 (en) * | 2007-12-12 | 2011-05-10 | Uop Llc | Aromatic isomerization catalyst and a process of use thereof |
EP2253607B1 (en) * | 2008-03-19 | 2012-06-20 | Toray Industries, Inc. | Method of converting ethylbenzene and process for producing p-xylene |
US9365468B2 (en) * | 2014-05-06 | 2016-06-14 | Uop Llc | Methods and systems for reforming and transalkylating hydrocarbons |
US20160122262A1 (en) * | 2014-10-31 | 2016-05-05 | Exxonmobil Chemical Patents Inc. | Xylene Isomerization Process with Sulfidation |
WO2018118208A1 (en) | 2016-12-21 | 2018-06-28 | Uop Llc | Composition of matter and structure of zeolite uzm-55 and use in isomerization of aromatic molecules |
EP3947325A1 (en) * | 2019-03-29 | 2022-02-09 | ExxonMobil Chemical Patents Inc. | Novel zeolite, process for making same, and use thereof in converting aromatic hydrocarbons |
CN112573983B (zh) * | 2019-09-29 | 2023-03-28 | 中国石油化工股份有限公司 | 一种由含乙苯的c8芳烃生产对二甲苯的方法 |
CN112573986B (zh) * | 2019-09-29 | 2023-05-05 | 中国石油化工股份有限公司 | 由c8芳烃生产对二甲苯的方法 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4341622A (en) * | 1980-12-04 | 1982-07-27 | Mobil Oil Corporation | Manufacture of benzene, toluene and xylene |
US4973784A (en) * | 1988-10-06 | 1990-11-27 | Mobil Oil Corp. | Process for reducing the durene content of effluent resulting from the catalytic conversion of C1 -C4 oxygenates to gasoline |
US5032561A (en) * | 1988-09-29 | 1991-07-16 | Teijin Petrochemical Industries, Ltd. | Catalyst composition for cracking non-aromatic hydrocarbons and isomerizing C8-aromatic hydrocarbons |
US5763720A (en) * | 1995-02-10 | 1998-06-09 | Mobil Oil Corporation | Transalkylation process for producing aromatic product using a treated zeolite catalyst |
RU2125977C1 (ru) * | 1995-04-24 | 1999-02-10 | Юоп | Способ каталитической изомеризации неравновесной смеси c8- ароматических углеводородов |
US6504076B1 (en) * | 2001-05-18 | 2003-01-07 | Fina Technology, Inc. | Method of conversion of heavy aromatics |
RU2233260C2 (ru) * | 2000-09-13 | 2004-07-27 | Юоп Ллк | Селективная изомеризация ксилолов и конверсия этилбензола |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3702886A (en) * | 1969-10-10 | 1972-11-14 | Mobil Oil Corp | Crystalline zeolite zsm-5 and method of preparing the same |
US4188282A (en) * | 1978-06-12 | 1980-02-12 | Mobile Oil Corporation | Manufacture of benzene, toluene and xylene |
JPS6035284B2 (ja) | 1981-01-27 | 1985-08-14 | 東レ株式会社 | ペンタシル型ゼオライトの製造法 |
JPS62228031A (ja) * | 1981-06-03 | 1987-10-06 | Toray Ind Inc | 芳香族炭化水素の変換方法 |
JPS5877828A (ja) * | 1981-11-02 | 1983-05-11 | Toray Ind Inc | エチルベンゼンを含むキシレン類の変換方法 |
CA1299588C (en) * | 1987-08-25 | 1992-04-28 | Kuniyuki Tada | Process for conversion of ethylbenzene in c _aromatic hydrocarbon mixture |
JPS6456626A (en) | 1987-08-25 | 1989-03-03 | Toray Industries | Method for converting ethylbenzene in 8c aromatic hydrocarbon mixture |
JP2801775B2 (ja) * | 1989-12-13 | 1998-09-21 | モービル・オイル・コーポレイション | C▲下9▼+芳香族原料の接触転化方法 |
US5401386A (en) * | 1992-07-24 | 1995-03-28 | Chevron Research And Technology Company | Reforming process for producing high-purity benzene |
JPH08143483A (ja) | 1994-03-03 | 1996-06-04 | Mitsubishi Oil Co Ltd | p−キシレンの製造方法及び装置 |
JPH08119882A (ja) * | 1994-10-07 | 1996-05-14 | Chevron Usa Inc | 不純トルエンの芳香族化及び選択的不均化の併用による高純度ベンゼン及びパラに富むキシレンの製造法 |
US6342649B1 (en) | 1995-05-10 | 2002-01-29 | Denim Engineering, Inc | Method for removing ethylbenzene from a para-xylene feed stream |
US5977429A (en) * | 1996-08-22 | 1999-11-02 | Eastman Chemical Company | Synthetic polyester absorbent materials |
US5942651A (en) | 1997-06-13 | 1999-08-24 | Mobile Oil Corporation | Process for converting C9 + aromatic hydrocarbons to lighter aromatic products by transalkylation in the prescence of two zeolite-containing catalysts |
FR2797593B1 (fr) * | 1999-08-19 | 2002-05-24 | Inst Francais Du Petrole | Catalyseur comprenant au moins une zeolithe de type structural nes et du rhenium et son utilisation en transalkylation d'hydrocarbures alkylaromatiques |
US7247762B2 (en) * | 2003-09-12 | 2007-07-24 | Exxonmobil Chemical Patents Inc. | Process for xylene isomerization and ethylbenzene conversion |
EP1699556A2 (en) * | 2003-12-30 | 2006-09-13 | Uop Llc | Process and catalyst for c8 alkylaromatic isomerization |
ITMI20040077A1 (it) * | 2004-01-22 | 2004-04-22 | Polimeri Europa Spa | Procedimento per la idrodealchilazione catalitica di idrocarburi alchilaromatici |
-
2007
- 2007-03-28 WO PCT/JP2007/056547 patent/WO2007114127A1/ja active Application Filing
- 2007-03-28 MY MYPI20083835A patent/MY153671A/en unknown
- 2007-03-28 TW TW096110677A patent/TWI432409B/zh not_active IP Right Cessation
- 2007-03-28 RU RU2008142763/04A patent/RU2448937C2/ru not_active IP Right Cessation
- 2007-03-28 KR KR1020087026319A patent/KR101357387B1/ko not_active IP Right Cessation
- 2007-03-28 US US12/295,006 patent/US20100179360A1/en not_active Abandoned
- 2007-03-28 EP EP07739985A patent/EP2008988A4/en not_active Withdrawn
- 2007-03-28 CN CN2007800113703A patent/CN101410354B/zh not_active Expired - Fee Related
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4341622A (en) * | 1980-12-04 | 1982-07-27 | Mobil Oil Corporation | Manufacture of benzene, toluene and xylene |
US5032561A (en) * | 1988-09-29 | 1991-07-16 | Teijin Petrochemical Industries, Ltd. | Catalyst composition for cracking non-aromatic hydrocarbons and isomerizing C8-aromatic hydrocarbons |
US4973784A (en) * | 1988-10-06 | 1990-11-27 | Mobil Oil Corp. | Process for reducing the durene content of effluent resulting from the catalytic conversion of C1 -C4 oxygenates to gasoline |
US5763720A (en) * | 1995-02-10 | 1998-06-09 | Mobil Oil Corporation | Transalkylation process for producing aromatic product using a treated zeolite catalyst |
RU2125977C1 (ru) * | 1995-04-24 | 1999-02-10 | Юоп | Способ каталитической изомеризации неравновесной смеси c8- ароматических углеводородов |
RU2233260C2 (ru) * | 2000-09-13 | 2004-07-27 | Юоп Ллк | Селективная изомеризация ксилолов и конверсия этилбензола |
US6504076B1 (en) * | 2001-05-18 | 2003-01-07 | Fina Technology, Inc. | Method of conversion of heavy aromatics |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2514423C1 (ru) * | 2010-03-31 | 2014-04-27 | Юоп Ллк | Способ изомеризации ксилола и этилбензола с использовнием uzm-35 |
Also Published As
Publication number | Publication date |
---|---|
TWI432409B (zh) | 2014-04-01 |
EP2008988A1 (en) | 2008-12-31 |
US20100179360A1 (en) | 2010-07-15 |
WO2007114127A1 (ja) | 2007-10-11 |
TW200745008A (en) | 2007-12-16 |
KR20080114824A (ko) | 2008-12-31 |
MY153671A (en) | 2015-03-13 |
KR101357387B1 (ko) | 2014-02-03 |
RU2008142763A (ru) | 2010-05-10 |
CN101410354B (zh) | 2012-07-25 |
CN101410354A (zh) | 2009-04-15 |
EP2008988A4 (en) | 2009-10-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
RU2448937C2 (ru) | Способ превращения этилбензола и способ получения пара-ксилола | |
US4899012A (en) | Catalyst for the isomerization of aromatics | |
RU2365573C1 (ru) | Двухстадийный способ изомеризации ароматических соединений | |
US7371913B2 (en) | Selective aromatics isomerization process | |
RU2514423C1 (ru) | Способ изомеризации ксилола и этилбензола с использовнием uzm-35 | |
US20080146859A1 (en) | Selective Aromatics Isomerization Process | |
US8273935B2 (en) | Selective aromatics isomerization process | |
EA001597B1 (ru) | Способ изомеризации алкилароматических углеводородов | |
US11845718B2 (en) | Process for producing p-xylene and ethylbenzene from C8 aromatic containing ethylbenzene | |
JP4735774B2 (ja) | エチルベンゼンの転化方法及びパラキシレン製造方法 | |
JP4830944B2 (ja) | エチルベンゼンの脱アルキル化及びキシレンの異性化二元機能触媒 | |
RU2727190C2 (ru) | Улучшенный катализатор превращения этилбензола в способе изомеризации ксилола | |
JP5292699B2 (ja) | エチルベンゼンの転化方法およびパラキシレンの製造方法 | |
JP4423577B2 (ja) | Euo型構造を有するゼオライトを含有する触媒を使用する8個の炭素原子を含有する芳香族留分の異性化方法 | |
RU2727174C2 (ru) | Каталитическая композиция, ее получение и способ применения указанной композиции | |
TWI490035B (zh) | 使用雙催化劑系統之芳香族化合物異構化 | |
WO2009075957A2 (en) | Molecular sieve and catalyst incorporating the sieve | |
JP2009084227A (ja) | ベンゼンの製造方法 | |
JPH10212251A (ja) | メタキシレンの製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20140329 |